Crew's first job was teaching English in Southern California.[2] Crew began his career as a school administrator in Worcester, Massachusetts.[7] He also worked in administrative positions in Boston, Massachusetts and was the assistant superintendent and superintendent of schools in Sacramento, California,[6] holding the latter position from 1988 to 1993.[2] He left to lead the school system at Tacoma, Washington, where test scores improved during his tenure, drawing the attention of the New York City Board of Education,which had had six chancellors in ten years.[2]

When looking at Crew’s student achievement record, some point to one-year drops in test scores as a picture of his overall record. The Abt report concluded that Tacoma’s 1995 increase in test scores was most likely a result of efforts to increase student test-taking skills, but Tacoma school officials believe the short-term gains were a result of Crew leaving for New York causing a setback in continued improvement.[8]Peter Sacks, an author and journalist, said that Crew is one of a breed of superintendent who focuses on short-term gains that may not be good for the district in the long-term.[9] However, in New York, reforms initiated during Crew’s tenure have been credited with playing a role in the continually improving test scores that his successors have achieved.[10]

There has been substantial academic research on changes to oversight in New York City that indicate Crew's creation of a more autonomous "Chancellor's District" was effective turning around failing schools.[13] In 2010, the Coalition for Educational Justice in New York City cited the Chancellor’s District and Crew's School Improvement Zone in Miami as a framework for their School Transformation Zone.[14]

During Crew's tenure, his administration was marred by a 1997 report by Edward F. Stancik, the Special Commissioner of Investigation, which questioned school administrators for not following procedures and delaying the report of a rape of a 14-year-old girl, which was the third instance in that high school. In response to the report, Crew initiated due process procedures to determine disciplinary action for the administrators involved.[15] Crew was later blamed for organizing efforts to remove independent oversight and engaging in a campaign to have Stancik removed by accusing him of exaggerating his reports saying they were overly dramatic and adversely affected the school system.[16]

After steadily rising for several years, math and science scores dropped in 1997, as a result of new tests and higher standards. At the time, Mayor Giuliani placed blame on the school board and the dysfunctional system itself.[17]

Crew also garnered controversy. His administration was involved in not reporting a crime and obstructing the investigation involving the sexual assault of a 14-year-old female student by a football player, who was later charged with lewd and lascivious assault on a minor.[9] A civil suit was brought against Crew by the former Miami-Dade County Public Schools Inspector General, Herbert Cousins, a former FBI agent who alleged Crew and his staff slandered and defamed him to obstruct his investigation and disclosure of illegal activities by Crew and some board members.[9]

Crew's critics pointed to an increase in “F” schools during 2007 that was actually a state-wide phenomenon caused by a change in the school grading formula.[25] The Greater-Miami Chamber of Commerce stated that Crew’s success was reflected in the District’s performance on the FCAT, which continues a trend that adds up to significant improvement over the last five years.[26]

In June 2008, the Miami Herald reported that Crew's School Improvement Zone generated few noteworthy achievements in its first year. One school board member stated, "We spent $100 million and it didn't do anything. To me, that's a complete failure."[27] Defenders of the program note that over the project's three-year history, substantial gains have been made, including the percentage of "D" and "F" schools dropping from 90% in 2005 to 22% in 2007.[28] One principal credited the initiative with helping her school raise its grade from a “D” to an “A” in three years.[24]

At a June 2008 Miami-Dade County school board meeting, Crew said the district had overspent millions of dollars during the past two years because it had hired more teachers than budgeted, lost state funding, and encountered rising costs.[29] School Board member Renier Diaz De La Portilla called for Crew's ouster, criticizing the way he has managed the schools' budget.[6][30]Ana Rivas Logan, another board member, called Crew "insubordinate."[30] At an August 4, 2008 school board meeting, the item to terminate Crew's contract failed. Despite Crew's strong support from business and community leaders,[31] the School Board bought out his contract at its September 10, 2008 meeting.

In 2009, the district's improved performance continued, and Miami high school students made greater gains than their peers statewide.[32] Crew’s secondary school reform initiative was credited by his successor for boosting the district’s high school graduation rate.[33]